Benzenepropanoic acid → HCID 54709996, compound

HRID 1620020Notes

Reaction equation

HRID 1620020 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[CH:14]=[C:13]([CH3:15])[O:12][C:11](=[O:16])[CH:10]=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:32](O)(=[O:41])[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.N#N>C(Cl)Cl.CN(C1C=CN=CC=1)C>[OH:8][C:9]1[CH:14]=[C:13]([CH3:15])[O:12][C:11](=[O:16])[C:10]=1[C:32](=[O:41])[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

8

Reactant 5

HCID 107Benzenepropanoic acidHCID 947NitrogenHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54709996HCID 54709996, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (1.12 ml; 8 mmol; Aldrich) was added to 4-hydroxy-6-methyl-2-pyrone (1.01 g; 8 mmol; Aldrich) in 60 ml CH2Cl2, and the reaction mixture was stirred under N2 for 10 min at 0° C. DMAP (293.3 mg; 2.4 mmol; Aldrich) and DCC (1.65 g; 8 mmol; Aldrich) were added, and the reaction mixture was stirred under N2 for 15 min at 0° C. Hydrocinnamic acid (1.20 g; 8 mmol; Aldrich) was added, and the reaction mixture was stirred N2 for 12 h at room temperature. The reaction mixture was filtered on celite to remove urea, acidified to pH ˜2 by addition of by 1 N HCl, diluted by addition of 60 ml water was added, and extracted with CH2Cl2 (2×100 ml). The organic layer was washed with brine, dried over anhydrous Na2SO4, and evaporated under vacuum. The product was isolated by chromatography on silica gel. Yield: 58%. MS (MALDI): calculated, m/z 259.1 (MH+); found, 259.1.

Workup

  1. stirringthe reaction mixture was stirred under N2 for 15 min at 0° C
  2. filtrationThe reaction mixture was filtered on celite
  3. customto remove urea
  4. additionacidified to pH ˜2 by addition of by 1 N HCl
  5. additiondiluted by addition of 60 ml water
  6. additionwas added
  7. extractionextracted with CH2Cl2 (2×100 ml)
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. customevaporated under vacuum
  11. customThe product was isolated by chromatography on silica gel

Sources & evidence

ORD record
ord-36b68decec02409fb5a160fb8ce66983
Source dataset
uspto-grants-2014_07
Patent number
US08772332B2

Reaction notes

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